TY - JOUR
T1 - Chemoselectivity and the Chan-Lam Coupling Reaction
T2 - Adding Amino Acids to Polymer-Coated Microelectrode Arrays
AU - Graaf, Matthew D.
AU - Moeller, Kevin D.
N1 - Funding Information:
We thank the National Science Foundation (CBET 1262176) for their generous support of our work.
Publisher Copyright:
© 2016 American Chemical Society.
PY - 2016/2/19
Y1 - 2016/2/19
N2 - (Chemical Equation Presented). The placement of a peptide onto a microelectrode array is frequently complicated by the presence of multiple nucleophiles in the peptide. In the work reported here, we have found that the Chan-Lam coupling reactions used to site-selectively place thiol, alcohol, and amine nucleophiles onto diblock-copolymer-coated surfaces are chemoselective for the placement of thiol and alcohol nucleophiles on the arrays. This means that cysteine- and serine-containing peptides can be placed onto an array without any need to protect the N terminus of the peptide. Furthermore, it was found that placement of thiol groups onto an array with the Chan-Lam reaction using optimized reaction times leads to complete coverage of the electrodes. The extent of this coverage can be controlled by varying the reaction time in a manner that allows for the construction of arrays with a gradient of peptide concentrations.
AB - (Chemical Equation Presented). The placement of a peptide onto a microelectrode array is frequently complicated by the presence of multiple nucleophiles in the peptide. In the work reported here, we have found that the Chan-Lam coupling reactions used to site-selectively place thiol, alcohol, and amine nucleophiles onto diblock-copolymer-coated surfaces are chemoselective for the placement of thiol and alcohol nucleophiles on the arrays. This means that cysteine- and serine-containing peptides can be placed onto an array without any need to protect the N terminus of the peptide. Furthermore, it was found that placement of thiol groups onto an array with the Chan-Lam reaction using optimized reaction times leads to complete coverage of the electrodes. The extent of this coverage can be controlled by varying the reaction time in a manner that allows for the construction of arrays with a gradient of peptide concentrations.
UR - http://www.scopus.com/inward/record.url?scp=84958999250&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.5b02656
DO - 10.1021/acs.joc.5b02656
M3 - Article
C2 - 26765206
AN - SCOPUS:84958999250
SN - 0022-3263
VL - 81
SP - 1527
EP - 1534
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 4
ER -